Ost-the-main



Patented Sept. 26, 1922..

UNITET? STATES PATENT OFFIOE.

IVIAI'I BOCKMU'HL, OF HOCHST-ON-THE-DIIAIN, AND ADOLF SCHWARZ, OF FRANKFORT- ON-THE-MAIN', GERTMANY, ASSIGNORS TO FARBWERKE VORMF MEISTER LUCIUS & BRUNING, OF HOGHST-ON-THE-IVEAIN, GERIVIANY, A CORPORATION OF GERM'ANY.

ALIIEHATIC DIALKYLAMINO ALKYL COMPOUNDS AND PROCESS OF MAKING SAME.

1N0 Drawing.

T 0 all 107107 it may concern Be it known that we, MAX BooKMi'n-IL and ADOLF SoHWAnz, citizens of Germany, residing at Hochst-on-the-Main, Germany, and Frankfort-on-the-Main, Germany, respectively, have invented certain new and useful improvements in Aliphatic Dialkylamino alkyl Conngounds and Processes of Making Same, of which the following is a specification.

According to our present invention, aliphatic dialkylaminoakyl compounds are obtained by causing alkalies to act upon molecular mixtures of halogen-alkyldialkylamines ortheir salts and the com pounds of the type R.GO.Cl-l.(ft ).1 l, wherein R and R represent hydrogen or an alkyl residue, and X stands for a radicle which renders the carbon atom in the alpha position acid, for instance, CN, C00 alkyl, COO aryl, CO alkyl, and CO aryl. The bodies thus obtained can be utilized as important and valuable parent material for the production of pharmaceutical preparations.

The following examples illustrate our invention:

oz Dic/ hylaminoetbylucctoacctic ct/tg Zcstcr.

1. 136 parts of chlorethyldiethylaminc are mixed with 130 parts of acetoacetic ethylester and there are then gradually introduced, while stirring, 57-58 parts of powdered caustic alkali which causes a lively reaction. After cooling, the mixture is stirred with benzene, the benzene solution is shaken with ammonia dried and subjected to fractional distillation. The diethylamino-ethyl acetoacetic ester distills over at 1232 135 under a pressure of 10 mm.

2. 1.1 1 parts of caustic alkali are gradually introduced into 261 parts of bromoethyldiethylamine hydrobromate and 130 parts of acetoacetic ethylester. The further treatment of the product is carried out as indicated in example 1.

Application filed September 13, 1921.

Serial No. 500,432.

130 parts'of acetoacetic ester and 57-58 parts of powdered caustic alkali. It boils at 124 C. under a pressure of 12 mm. 4.. Dietitg lamnobutyZ-acetoacetic GZJLil/ZGSMT.

This compound is obtained in an analogous manner as that described in example 1) from 164- parts of diethylaminochlorobutanol cm CQHQQ'N. 01120112. c n

01 130 parts of aceto acetic ester and 57-58 parts of powdered caustic alkali. It boils at 138 (1. under a pressure of 10 mm.

Having now described our invention, what we claim is:

1. The process of producing dialkylaminoalkyl compounds, which consists in causing caustic alkalies to act upon the molecular mixtures of halogen alkyl dialkylamines or their salts and bodies ofthe general formula:

RUQCH (R .X wherein R and R represent hydrogen or an alkyl residue, and X represents a radicle which renders the carbon atom in the alpha position acid.

2. As new products new compounds of the type:

R.CO.OR (R ).X wherein R represents any dialkyiaminoalkyl residue and 1t and R, represent hydro gen or an alkyl residue, and 231 represents a radicle which renders the carbon atom in the alpha position acid.

In testimony whereof, we aflix our signatures.

Signed at Munich.

MAX BOCKM UHL.

Signed at Frankfort-on-the-ldain b' ADOLF SCHWARZ. 

